Triphenylphosphine → alpha-Oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester

HRID 2225723Notes

Reaction equation

HRID 2225723 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][CH2:22][CH2:23]O)[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:23][CH2:22][CH2:21][CH2:20][C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 134191363-Pyridinebutanol

Product 1

HCID 53999955alpha-Oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl esterYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.14 g), 3-pyridinebutanol (1.04 g), triphenylphosphine (2.07 g), and tetrahydrofuran (25 mL) was stirred at 0° C. while adding dropwise a solution of diethyl azodicarboxylate (1.37 g) in tetrahydrofuran (10 mL). The mixture was stirred for 2 hours at 0° C. and evaporated to dryness. The material was purified by HPLC (hexane-acetone; 2:1) to provide 1.4 g of alpha-oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester (4:1) molar hydrate as a colorless oil.

Workup

  1. stirringThe mixture was stirred for 2 hours at 0° C.
  2. customevaporated to dryness
  3. customThe material was purified by HPLC (hexane-acetone; 2:1)

Sources & evidence

ORD record
ord-c638c51050244ca5a59c36e99b3171d4
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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